Tips For Wearing A Hat


Wearing a hat has always been one of my favorite styling tricks. They keep you warmer in the winter, they provide some shade in the summer, and they cover troublesome hair. I own fedoras, Panamas, roll brim, straw and felt ones but no ball caps, cloches, boaters, buckets, beanies or Newsboy caps. Keep reading to learn why.






A hat makes a bold statement, so I keep the neckline open and never wear a necklace with a hat. I wear earrings mostly to cover the hole in my ears, never large eye-catching ones with a hat. Too many accessories always take a look in the wrong direction.






We visited First Watch on Sunday. It is a delightful daytime cafe serving fresh healthy options for breakfast or lunch only.






I had the Frittata Rustica which is a classic Italian-style omelet with kale, house-roasted Crimini mushrooms, onions and tomatoes topped with Mozzarella and Parmesan cheese. Served with ciabatta toast and a salad. It was excellent!






Mr. Mickey had the Floridan French Toast made from thick-cut brioche with wheat germ and powdered cinnamon sugar, covered with fresh banana, kiwi and seasonal berries.






My super casual and comfortable look included a fedora style hat from J.Jill. A relaxed cotton shirt from Everlane here. I did not tuck in any part of the shirt since I am wearing pull-on style ankle jeans from Liverpool Jeans Co. here. The tote bag was on my shopping site last year, similar here. The Born sandals are from last year, similar here. Similar sunglasses here.


The hat styles shown below are NOT the right choice for my face shape. These hats make my face look much more round because they have rounded crowns or rest on the top of the head and add width.

The hats shown below are better choices for me because they have a brim that is not too wide and a crown that does not rest on the top of my head to flatten my hair. I need some height at the crown, be it a hat or a hairstyle. I never repeat the roundish shape of my face in accessories, collars, or hairstyles.


All the hat images are shopable links. As always, links in my blog posts may generate a small commission for Susan After 60 Inc.


If you have followed my journey for a while, you know that I am not an expert on anything. I do read a lot and enjoy doing research more than most people. I share what I learn in the hopes that it helps you to use my examples to figure out what works best for you. Looking and feeling your best is the first step to enjoying a full and healthy second fifty years with confidence. I hope you have a delightful weekend!



Without external investment, I created this site to honor and serve women of all ages. The shopping site here provides classic basics and accessories which you can wear in a variety of ways. Ongoing studies include trends and style advice from image and nutrition experts so that the tips I share with you are never just me sharing my opinion. I use art and science to inspire your outfit selections and to help you stretch your wardrobe possibilities while looking your best. SusanAfter60.com is an online space where women can share their thoughts, ask questions, gather style tips, gain local travel inspiration, and learn more about nutrition.


Susan Street

Blogger for SusanAfter60.com

32 Comments
  1. Hats…..one of my big dilemmas. I’m short (5’1”) and fluffy. I have a very small head and hats make me feel like I look like a mushroom. I would LOVE to be able to pull off wearing a hat. Advice? Tips?

  2. Susan, this close analysis of hat shapes in relation to face shapes is wonderful and helpful. I can appreciate your reason for not wearing a ball cap, and I’m adding one of my own, which is highly opinionated: I think ball caps are among the ugliest hats ever invented. Fine for ball players while they are playing, awful for everyone else. I simply cannot comprehend why the craze for them persists. There! I’ve gotten that off my chest! Thank you for all your useful remarks on shapes and styles of clothing and accessories, (always offered in a more courteous tone than I have used for this rant about ball caps). You have already improved my small wardrobe and my attention to how I present myself even when going out on errands in my very small town.

  3. Lovely outlook to wearing hats. I am with you Susan, in that the style of hat should complement the shape of our face. My problem is that I have a small head for hats, and children’s sizes just look silly – so the search goes on. Would it not be great if ladies started wearing hats regularly àgain?
    The breakfasts look amazing. Thank you for sharing. Have a great weekend both of you.

  4. Mr. Mickey’s French toast looks scrumptious. I love it made with brioche bread. I’ve never worn hats but as my skin is aging along with the rest of me, I’m beginning to think they have a purpose. Thanks for the primer.

  5. Susan,

    I get really bad “hat hair” when I wear a hat. I was just wondering – did you leave your hat on when you ate in the restaurant, or did you take it off?

    1. Take your fashion hat off only if it blocks someone’s view, such as at a wedding or in a theater. Do not wear a hat indoors at work.
      Only remove unisex hats, such as baseball caps when you go indoors.

  6. Thanks for your post. I love the Belmar hat!
    I noticed that the images of the hats you like are all summer/warm weather hats. What do you recommend for winter/cold weather hats for round faces?

    I enjoy your blog which has been so helpful.

    Kathy

  7. I would love to see a winter hat tutorial. Where I live, winter hats must cover ears snugly and protect from frostbite. Do I chose a slouchy hat, a toque…? Style goes out the window at times like these.

  8. I love this look, Susan. Thank you for including a site to order the tote. It’s on sale and with in-store pick up I avoided shipping. You’re so great!

  9. How do you keep,from getting hathair in warm weather. With our heat an h7midity in Southeast Louisiana, my hair always turns into a flat gooey mess if I wear a hat in summer. I love them but they don’t love me.

  10. Last year i bought a man’s straw fedora for my husband, but it was too small. I’ve been wearing it and have gotten many compliments…especially from other men. It’s a little large on me, which means I don’t get bad hat hair. I love it!

  11. Your advice has been so helpful and I look forward to your daily posts. I have purchased several scarves from your site and one of the Shapeez. I enjoy your adventures with Mr Mickey. You make a beautiful couple. You are loving life!

  12. I have never felt like I looked even passable in a hat, but now I’m wondering if I have just not tried the best style for my round face. As always, Susan, your advice has inspired me.

  13. I am always hesident about wearing a hat. I too am 5’1” and had read years ago that hats can actually make us (petite) appear shorter. I believe this can be the case because I have noticed how certain hats on small women do make them seem less tall and top heavy so to speak…..out of proportion. I would appreciate your take on this because you are so very savvy on such fashion details.

  14. Interesting and helpful post! I always enjoy your arrival in my inbox and appreciate the thought and work that you (and Mr Mickey) put into all your posts.

    I love hats but I wear glasses and felt that they detracted from the look, whereas sunglasses with a hat look OK. Strange! I solved the problem by getting a slightly blue tint to the lenses of my ordinary glasses. I can’t explain why but it makes such a difference.

    Like you, I look better in a hat with a brim. When it rains (most of the time in the UK!) I wear a waterproof leather fedora with my trench coat and it looks great – better than a leave-it-behind umbrella.

  15. Just wish hats came in a larger size to accommodate those of us who have lots of hair and a large head. There are a few, but not many. Ughhhh!

  16. I also love hats and wear one almost daily. Love your hat and again as usual the food looks yummy too. I especially like Mr. Mickey ‘s.

  17. Your pants are so cute on you! Do you order your regular size in this brand? The Liverpool Co. pictures make the jeans look extremely clingy so I’m hesitant. Yours look perfect.

  18. Really appreciate your styling tips. At 76 years old I’ve decided to get more style in my clothing choices.
    I still have my natural brown hair which helps me look younger than I am from what people tell me.

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I blogged for five years as Fifty, not Frumpy. Now that I am in my sixties, I am honoring this new decade with a great new website and shop SusanAfter60.com

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